Acetaldehyde → 1-(6-Methoxypyridin-3-yl)ethanol

HRID 859730Notes

Reaction equation

HRID 859730 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[Li]CCCC.[CH:15](=[O:17])[CH3:16]>CCOCC>[CH3:9][O:8][C:5]1[N:6]=[CH:7][C:2]([CH:15]([OH:17])[CH3:16])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 27348955-Bromo-2-methoxypyridineHCID 178418339Butyllithium

Product 1

HCID 450909001-(6-Methoxypyridin-3-yl)ethanolYield 91%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 5-bromo-2methoxy-pyridine (19.3 g, 193 mmol) in anhydrous Et2O (200 mL) at −78° C. was added n-BuLi (2.5 M in hexanes, 50 mL) over 30 min. The resulting mixture was stirred at that temperature for addition 30 min before acetaldehyde (5 mL) was added. The reaction was slowly warmed up to room temperature and the solvent was removed in vacuo. The residue was purified by flash column chromatography to afford the desired product (14.3 g, 91% yield). 1H NMR (400 MHz, CDCl3): δ 1.50 (d, J=8.0 Hz, 3 H), 3.93 (s, 3 H), 4.87–4.92 (m, 1 H), 6.75 (d, J=8.0 Hz, 3 H), 7.63–7.66 (m, 1 H), 8.12–8.14 (m, 1 H).

Workup

  1. additionwas added
  2. customthe solvent was removed in vacuo
  3. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-0219a6c169164edd857d4e7274473df3
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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